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EP1419047B1 - Procede pour produire une mince couche d'informations fluorescente sur la surface en relief d'un support - Google Patents

Procede pour produire une mince couche d'informations fluorescente sur la surface en relief d'un support Download PDF

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Publication number
EP1419047B1
EP1419047B1 EP02739430A EP02739430A EP1419047B1 EP 1419047 B1 EP1419047 B1 EP 1419047B1 EP 02739430 A EP02739430 A EP 02739430A EP 02739430 A EP02739430 A EP 02739430A EP 1419047 B1 EP1419047 B1 EP 1419047B1
Authority
EP
European Patent Office
Prior art keywords
composition
poly
group
fluorescent
ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP02739430A
Other languages
German (de)
English (en)
Other versions
EP1419047A1 (fr
EP1419047A4 (fr
Inventor
Galina Dorozhkina
Aleksei Lezhnev
Eugene Levich
Dmitry Pebalk
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
D Data Inc
Original Assignee
D Data Inc
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Filing date
Publication date
Application filed by D Data Inc filed Critical D Data Inc
Publication of EP1419047A1 publication Critical patent/EP1419047A1/fr
Publication of EP1419047A4 publication Critical patent/EP1419047A4/fr
Application granted granted Critical
Publication of EP1419047B1 publication Critical patent/EP1419047B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/2403Layers; Shape, structure or physical properties thereof
    • G11B7/24035Recording layers
    • G11B7/24038Multiple laminated recording layers
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26Apparatus or processes specially adapted for the manufacture of record carriers
    • G11B7/266Sputtering or spin-coating layers

Definitions

  • the present invention is related to a method of manufacturing a multilayer fluorescent information carrier and more particular to the method utilizing a mixture of organic solvents for a photopolymeric composition (PPC).
  • PPC photopolymeric composition
  • optical memory media with multiple layers have been developed.
  • parasitic reflection can occur at layer boundaries. That reflection and the resulting interference impair reading.
  • Examples of such devices, utilizing the multiplayer fluorescent carrier are disclosed in U.S. Pat. No.6,039,898 and in WO 99/47327 .
  • Such carriers exhibit high recording density, contrast, and signal-to -noise ratio. It is common to use fluorescent recording materials that, when exposed to reading light at one wavelength, fluoresce at a different wavelength. The problem of parasitic reflection can be solved by filtering out reflected light at the reading wavelength. Also, since the fluorescent light is incoherent, there is no problem of interference.
  • the multilayer fluorescent information carrier comprises a photopolymerizable composition applied to a solid base having a relief pattern. A transparent film layer is applied on top of the photopolymerized composition. The three layers are spun in a centrifuge to cause a thin, even distribution of the photopolymerizable composition, which is photopolymerized. The resulting replica is separated from the relief pattern and has a fluorescent material applied thereto. Alternatively, the replica has a non-fluorescent material applied thereto, and the non-fluorescent material is made fluorescent through diffusion. Multiple information layers thus formed can be glued together to form a multilayer storage medium.
  • the principal object of the invention comprises the utilization of a mixture of at least one ketone having a boiling temperature in the range of 98-120 °C with one or more other solvents having a boiling temperature of about 80 °C or lower. This mixture is used for the photopolymeric composition (PPC) with the fluorescent dye.
  • PPC photopolymeric composition
  • a thin-layer fluorescent polymer coated with distributed fixed luminescent centers can be prepared by using photosolidified liquid polymer compositions containing luminophores.
  • a composition is spin-coated forming a thin liquid film distributed across the replica surface in conformity with the shape of its relief and consisting predominantly of photosolidified, generally by cation and/or radial mechanisms, monomers and oligomers and dopants determining spectral and luminescent, physical and mathematical, adhesive and other characteristics of the polymer coat following its solidification by UV light.
  • the liquid composition applied should possess a good spreadability on the replica surface, high adhesion, and ease of forming a liquid and solidified film uniformely spread on the surface and differentially in terms of the replica relief, which can be attained through using a specific composition as well as coating and solidification conditions.
  • Photosolidification of the composition results in a bilayer structure with a polymeric replica and thin-film fluorescent polymer coat.
  • the bilayer structure represents as a unit a single layer a fluorescent information carrier. From similarly generated single layer carriers, there can be fabricated multilayer fluorescent information carriers of various types by sealing them together.
  • a liquid composition for a thin-film polymer fluorescent information layer (IL) according to the present invention comprises:
  • the organic solvent includes a mixture of at least one ketone with another solvent.
  • Polymeric substance is prepared by mixing components consisting of Bis (3,4-epoxycyclohexylmethyl) adipate (60% wt.) and Neopentylglycoldiglycidyl ether (40% wt.).
  • the fluorescent dye (FD) Oxazine-1 is added to the PS in the amount of 0,02 mol/l.
  • the mixture of solvents consisting of 10% wt. of isobutyl-methylketone, 50% wt. of 3- methyl-2-butanone and 40% wt. of 2-propanol are prepared.
  • the PS-FD composition is dissolved in the mixture of the solvents at the temperature of 60°C degree stirred for 4 hours to obtain a homogenous 4% wt. solution.
  • the 6 pph mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) in ratio to the PS were applied.
  • the obtained solution is filtered and applied to the PPC-replic
  • Rhodamine-700 in amount 0.025 mol/l and 0.005 mol/l Rhodamine-800 are used as the fluorescent dye.
  • PS-FD concentration was 1.42 % wt.
  • the 4 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) and 6 pph mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) (4 % wt) are used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l is used as the fluorescent dye.
  • PS-FD concentration was 3.3 % wt. Fluorescent signal-to-noise ratio was 10-12 for the DVD-replica.
  • the 6 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) is used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l is used as the fluorescent dye.
  • PS-FD concentration was 2.5 % wt.
  • a mixture of 28.6 % wt 3-methyl-2-butanone and 71.4 % wt methyl acetate is used as solvent.
  • the 4 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) and mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) (4 % wt) in ratio to PS are used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l and 0.005 mol/l Rhodamine-800 are used as the fluorescent dye.
  • PS-FD concentration was 1.42 % wt.
  • the 4 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) and mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) (4 % wt) in ratio to PS are used as the photopolymerization initiator.
  • Mixture of 0.015 mol/l Oxazine-1 and Rhodamine-700 in amount 0.025 mol/l and 0.005 mol/l Rhodamine-800 are used as the fluorescent dye.
  • PS-FD concentration was 1.67 % wt.
  • a mixture of 40 % wt 3-methyl-2-butanone and 60 % wt methyl chlorophorm is used as solvent.
  • 1-Chloro-4-propoxy-9H-thioxanthen-9-one in ratio to the catalyst weight are used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l and 0.005 mol/l Red-300 (Basf) (a dye based on perylene-1,6,7,12-tetraphenoxy-3,4,9,10-tetracarboxylic acid bis(2,6-diisopropylanilide)) are used as the fluorescent dye.
  • PS-FD concentration was 2 % wt.
  • the 4 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) and mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) (4 % wt) in ratio to PS are used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l is used as the fluorescent dye.
  • PS-FD concentration was 2.5 % wt.
  • the 4 pph mixed Triarylsulfonium Hexafluoroantimonate salt (50 % wt solution in propylene carbonate) and mixed Triarylsulfonium Hexafluorophosphate salt (50% wt. solution in propylene carbonate) (4 % wt) in ratio to PS are used as the photopolymerization initiator.
  • Rhodamine-700 in amount 0.025 mol/l is used as the fluorescent dye.
  • PS-FD concentration was 2.5 % wt.

Landscapes

  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Epoxy Resins (AREA)
  • Manufacturing Optical Record Carriers (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
  • Polymerisation Methods In General (AREA)
  • Length Measuring Devices By Optical Means (AREA)
  • Magnetic Record Carriers (AREA)

Claims (9)

  1. Procédé de fabrication d'une couche mince d'informations fluorescente sur la surface en relief d'un support comprenant les étapes consistant à :
    (a) fournir une composition photopolymérique comprenant une substance polymérisable (PS) et un colorant fluorescent (FD) ;
    (b) fournir un mélange solvant comprenant au moins une cétone ;
    (c) dissoudre la composition obtenue dans le mélange solvant de solvants ;
    (d) ajouter un photo-initiateur de polymérisation à la composition résultante ;
    (e) filtrer la composition de l'étape (d) ; et
    (f) appliquer ladite composition à la surface dudit support.
  2. Procédé selon la revendication 1, dans lequel la substance polymérisable (PS) est choisie parmi le groupe consistant en bis (3,4-époxycyclohexylméthyl) adipate, néopentyl glycol diglycidyl éther; triméthylol propanetriglicidyl éther, diéthylène glycol, 3,4-époxycyclohexylméthyl-3,4-époxycyclohexane carboxylate, triméthylolpropane trivinyl éther, ε-caprolactone triol, poly(vinylchlorure-co-vinylacétate-co-2-hydroxypropyl acrylate) hydroxyle, poly(o-crésyl glycidyl éther) co-formaldehyde, époxyde cycloaliphatique 4206, poly(vinylchlorure-co-isobutyl vinyl éther et poly(vinylformal).
  3. Procédé selon les revendications 1 et 2, dans lequel le mélange solvant comprend une ou plusieurs cétones choisies parmi le groupe consistant en isobutyl-méthylcétone, 3-méthyl-2-butanone, acétone, méthyl éthyl cétone et leurs mélanges.
  4. Procédé selon les revendications 1 et 2, dans lequel le mélange solvant comprend l'isobutylcétone.
  5. Procédé selon la revendication 1, dans lequel le photo-initiateur de polymérisation dans l'étape (d) est choisi parmi le groupe consistant en sel d'hexafluorophosphate de triarylsulfonium et/ou sel d'hexafluoroantimonate de triarylsulfonium.
  6. Procédé selon la revendication 1, dans lequel le colorant fluorescent (FD) est choisi parmi le groupe consistant en oxazine-1, rhodamine-700, rhodamine-800 et l'acide bis(2,6-diisopropylanilide) pérylène-1,6,7,12-tétraphénoxy-3,4,9,10-tétracarboxylique.
  7. Procédé selon les revendications 1 à 6, dans lequel les solvants sont choisis parmi le groupe consistant en cétones ayant une température d'ébullition de 98°C à 120°C et d'autres solvants ayant la température d'ébullition non supérieure à environ 80°C.
  8. Procédé selon les revendications 1 à 7, dans lequel la dissolution de la composition PS-FD est réalisée en agitant ladite composition pendant quatre heures à 60°C pour obtenir une solution homogène à 4 %.
  9. Procédé selon les revendications 1 à 8, comprenant un support d'information fluorescent multicouche, dans lequel chaque couche est informée séparément et reliée conjointement sous forme d'une unité.
EP02739430A 2001-05-29 2002-05-29 Procede pour produire une mince couche d'informations fluorescente sur la surface en relief d'un support Expired - Lifetime EP1419047B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29353701P 2001-05-29 2001-05-29
US293537P 2001-05-29
PCT/US2002/016687 WO2002096633A1 (fr) 2001-05-29 2002-05-29 Procede pour produire une mince couche d'informations fluorescente sur la surface en relief d'un support

Publications (3)

Publication Number Publication Date
EP1419047A1 EP1419047A1 (fr) 2004-05-19
EP1419047A4 EP1419047A4 (fr) 2006-10-25
EP1419047B1 true EP1419047B1 (fr) 2008-07-02

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Family Applications (1)

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EP02739430A Expired - Lifetime EP1419047B1 (fr) 2001-05-29 2002-05-29 Procede pour produire une mince couche d'informations fluorescente sur la surface en relief d'un support

Country Status (5)

Country Link
EP (1) EP1419047B1 (fr)
JP (1) JP2004532726A (fr)
AT (1) ATE400053T1 (fr)
DE (1) DE60227378D1 (fr)
WO (1) WO2002096633A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9275671B2 (en) 2011-06-09 2016-03-01 Case Western Reserve University Optical information storage medium

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62246784A (ja) * 1986-04-21 1987-10-27 Canon Inc 光記録媒体
US5669995A (en) * 1996-01-29 1997-09-23 Hong; Gilbert H. Method for writing and reading data on a multi-layer recordable interferometric optical disc and method for fabricating such
US6039898A (en) * 1997-05-08 2000-03-21 O.M.D. Optical Memory Devices, Ltd. Optical memory device and a method for manufacturing thereof
US7226637B2 (en) * 2000-01-18 2007-06-05 D Data Inc. Manufacturing method for multilayer fluorescent information carriers

Also Published As

Publication number Publication date
EP1419047A1 (fr) 2004-05-19
EP1419047A4 (fr) 2006-10-25
JP2004532726A (ja) 2004-10-28
DE60227378D1 (de) 2008-08-14
WO2002096633A1 (fr) 2002-12-05
ATE400053T1 (de) 2008-07-15

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